Methyl Isocyanate → HCID 67030708, compound

HRID 1959976Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:25])=[C:8](C(OC(C)(C)C)=O)[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH3:26][N:27]=[C:28]=[O:29]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:25][C:28]([NH:27][CH3:26])=[O:29])=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 12228Methyl Isocyanate

HCID 58271024HCID 58271024, compound

Product 1

HCID 67030708HCID 67030708, compoundYield 74%

Procedure

Following general method 4, employing 3-amino-1-(3-fluorophenyl)-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester and methyl isocyanate, afforded the title compound as a white solid (194 mg, 74%); LCMS (method B): RT=3.38 min, M+H+=306; 1H NMR (CDCl3, 300 MHz): 8.42 (s, 1H), 7.64 (d, J=2.7 Hz, 1H), 7.46 (d, J=2.7 Hz, 1H), 7.39 (dt, J=8.2, 6.2 Hz, 1H), 7.24-7.20 (m, 1H), 7.15 (dt, J=9.9, 2.3 Hz, 1H), 6.99 (tdd, J=8.3, 2.4, 0.9 Hz, 1H), 4.71-4.65 (m, 1H), 4.31 (q, J=7.1 Hz, 2H), 2.90 (d, J=4.9 Hz, 3H), 1.37 (t, J=7.1 Hz, 3H).

Sources & evidence

ORD record: ord-8cb577291629450eb083fa9569d2cac2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410279B2

Reaction notes

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